ES2365159T3 - Procedimiento para la reducción enzimática enantioselectiva de cetocompuestos. - Google Patents

Procedimiento para la reducción enzimática enantioselectiva de cetocompuestos. Download PDF

Info

Publication number: ES2365159T3
Authority: ES; Spain
Prior art keywords: alkyl; straight; methyl; branched chain; ethyl
Prior art date: 2005-09-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES06762851T

Other languages

English (en)

Spanish (es)

Inventor

Antje Gupta

Anke Tschentscher

Maria Bobkova

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cambrex IEP GmbH

Original Assignee

IEP GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-09-23

Filing date

2006-07-27

Publication date

2011-09-23

2006-07-27 Application filed by IEP GmbH filed Critical IEP GmbH

2011-09-23 Application granted granted Critical

2011-09-23 Publication of ES2365159T3 publication Critical patent/ES2365159T3/es

Status Active legal-status Critical Current

2026-07-27 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title claims abstract description 34
230000009467 reduction Effects 0.000 title claims abstract description 20
230000002255 enzymatic effect Effects 0.000 title claims abstract description 17
102000004316 Oxidoreductases Human genes 0.000 claims abstract description 27
108090000854 Oxidoreductases Proteins 0.000 claims abstract description 25
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims abstract description 21
CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 claims abstract description 20
230000002051 biphasic effect Effects 0.000 claims abstract description 16
150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 16
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims abstract description 14
125000000468 ketone group Chemical group 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
239000000203 mixture Substances 0.000 claims abstract description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
ZDVJGWXFXGJSIU-UHFFFAOYSA-N 5-methylhexan-2-ol Chemical compound CC(C)CCC(C)O ZDVJGWXFXGJSIU-UHFFFAOYSA-N 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
239000007788 liquid Substances 0.000 claims abstract description 10
ZWILTCXCTVMANU-UHFFFAOYSA-N 1,1,3-trichloropropan-2-one Chemical compound ClCC(=O)C(Cl)Cl ZWILTCXCTVMANU-UHFFFAOYSA-N 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 claims abstract description 5
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 claims abstract description 5
CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 claims abstract description 4
UDNZDMGFDFBONM-UHFFFAOYSA-N 1,4-dichlorobutan-2-one Chemical compound ClCCC(=O)CCl UDNZDMGFDFBONM-UHFFFAOYSA-N 0.000 claims abstract description 4
XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims abstract description 4
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims abstract description 4
ATPFRGQBOVFFQM-WJIDAKASSA-N [(1s,3r,7r,8r,8as)-3-(hydroxymethyl)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate Chemical compound C([C@@H]1[C@H](C)C=CC2=C[C@H](CO)C[C@@H]([C@@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 ATPFRGQBOVFFQM-WJIDAKASSA-N 0.000 claims abstract description 4
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims abstract description 4
QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 claims abstract description 4
229940117360 ethyl pyruvate Drugs 0.000 claims abstract description 4
230000000813 microbial effect Effects 0.000 claims description 3
241000186660 Lactobacillus Species 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
229940039696 lactobacillus Drugs 0.000 claims description 2
241000894006 Bacteria Species 0.000 claims 2
240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
241000235644 Issatchenkia Species 0.000 claims 1
241001112724 Lactobacillales Species 0.000 claims 1
241000235652 Pachysolen Species 0.000 claims 1
241000235648 Pichia Species 0.000 claims 1
230000008569 process Effects 0.000 abstract description 15
LVSQXDHWDCMMRJ-UHFFFAOYSA-N 4-hydroxybutan-2-one Chemical compound CC(=O)CCO LVSQXDHWDCMMRJ-UHFFFAOYSA-N 0.000 abstract description 4
102000004190 Enzymes Human genes 0.000 description 28
108090000790 Enzymes Proteins 0.000 description 28
-1 keto compound Chemical class 0.000 description 28
BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 19
229950006238 nadide Drugs 0.000 description 19
239000005515 coenzyme Substances 0.000 description 14
230000008929 regeneration Effects 0.000 description 14
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238000006243 chemical reaction Methods 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
229930194542 Keto Natural products 0.000 description 10
108010021809 Alcohol dehydrogenase Proteins 0.000 description 9
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229940055022 candida parapsilosis Drugs 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 8
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 8
108010031132 Alcohol Oxidoreductases Proteins 0.000 description 7
102000007698 Alcohol dehydrogenase Human genes 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
241001304302 Kuraishia capsulata Species 0.000 description 6
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000011534 incubation Methods 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
102000005751 Alcohol Oxidoreductases Human genes 0.000 description 5
238000004821 distillation Methods 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
230000001419 dependent effect Effects 0.000 description 4
108010084715 isopropanol dehydrogenase (NADP) Proteins 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
150000003333 secondary alcohols Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000186864 Weissella minor Species 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
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FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
108020005199 Dehydrogenases Proteins 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
240000001929 Lactobacillus brevis Species 0.000 description 2
235000013957 Lactobacillus brevis Nutrition 0.000 description 2
241001468191 Lactobacillus kefiri Species 0.000 description 2
241000186604 Lactobacillus reuteri Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241000187561 Rhodococcus erythropolis Species 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
101710197978 NADPH-dependent oxidoreductase Proteins 0.000 description 1
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125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011942 biocatalyst Substances 0.000 description 1
230000002210 biocatalytic effect Effects 0.000 description 1
230000036983 biotransformation Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
ZAJNMXDBJKCCAT-RXMQYKEDSA-N ethyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@@H](O)CCl ZAJNMXDBJKCCAT-RXMQYKEDSA-N 0.000 description 1
YERWBBMSDMSDKT-UHFFFAOYSA-N ethyl 2-oxopentanoate Chemical compound CCCC(=O)C(=O)OCC YERWBBMSDMSDKT-UHFFFAOYSA-N 0.000 description 1
UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 1
NPJCCMWYKLAISW-UHFFFAOYSA-N ethyl 8-chloro-6-oxooctanoate Chemical compound CCOC(=O)CCCCC(=O)CCCl NPJCCMWYKLAISW-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002496 iodine Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000019525 primary metabolic process Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000024053 secondary metabolic process Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007250 stereoselective catalysis Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

ES06762851T 2005-09-23 2006-07-27 Procedimiento para la reducción enzimática enantioselectiva de cetocompuestos. Active ES2365159T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT0157005A AT502185B1 (de)	2005-09-23	2005-09-23	Verfahren zur enantioselektiven enzymatischen reduktion von ketoverbindungen
ATA1570/2005		2005-09-23

Publications (1)

Publication Number	Publication Date
ES2365159T3 true ES2365159T3 (es)	2011-09-23

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ID=37102120

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ES06762851T Active ES2365159T3 (es)	2005-09-23	2006-07-27	Procedimiento para la reducción enzimática enantioselectiva de cetocompuestos.

Country Status (14)

Country	Link
US (1)	US20080233619A1 (de)
EP (1)	EP1926821B1 (de)
JP (1)	JP2009508499A (de)
KR (1)	KR101345252B1 (de)
CN (1)	CN101273136A (de)
AT (2)	AT502185B1 (de)
CA (1)	CA2621306C (de)
DE (1)	DE502006009367D1 (de)
DK (1)	DK1926821T3 (de)
ES (1)	ES2365159T3 (de)
PL (1)	PL1926821T3 (de)
PT (1)	PT1926821E (de)
SI (1)	SI1926821T1 (de)
WO (1)	WO2007036257A1 (de)

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US7879585B2 (en) *	2006-10-02	2011-02-01	Codexis, Inc.	Ketoreductase enzymes and uses thereof
TWI601825B (zh) *	2007-09-27	2017-10-11	Ｉｅｐ有限公司	對映異構選擇性酶催化還原中間產物之方法
EP2226386A1 (de)	2009-03-05	2010-09-08	IEP GmbH	Verfahren zur stereoselektiven enzymatischen Reduktion von Ketoverbindungen
WO2010150946A1 (en)	2009-06-22	2010-12-29	Sk Holdings Co., Ltd.	Method for preparation of carbamic acid (r)-1-aryl-2-tetrazolyl-ethyl ester
US8404461B2 (en)	2009-10-15	2013-03-26	SK Biopharmaceutical Co. Ltd.	Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
CN105481645B (zh) *	2015-12-01	2017-12-15	浙江科技学院	一种(s)‑1,1,1‑三氟‑2‑丙醇的合成方法
CN113784945A (zh) *	2018-12-22	2021-12-10	马拉迪制药有限公司	制备R-苯基乙酰基甲醇和β-氨基醇的新方法

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DE4014573C1 (de) *	1990-05-07	1991-10-10	Forschungszentrum Juelich Gmbh, 5170 Juelich, De
US5225339A (en) *	1992-02-26	1993-07-06	The Scripps Research Institute	Lactobacillus kefir alcohol dehydrogenase
CA2117482C (en) *	1992-03-13	2005-02-15	Maria-Regina Kula	New ketonic ester reductases, its preparation and use for enzymatic redox reactions
JP3574682B2 (ja) *	1993-09-24	2004-10-06	ダイセル化学工業株式会社	新規な酵素、該酵素を製造する方法、該酵素をコードするｄｎａ、該ｄｎａを含む形質転換体、該酵素による光学活性アルコール等の製造方法
JPH08266292A (ja) *	1995-03-31	1996-10-15	Fuji Oil Co Ltd	光学活性アルコールの製造方法
JP3766465B2 (ja) *	1996-02-29	2006-04-12	天野エンザイム株式会社	光学活性な２級アルコールの製造法
DE10119274A1 (de) *	2001-04-20	2002-10-31	Juelich Enzyme Products Gmbh	Enzymatisches Verfahren zur enantioselektiven Reduktion von Ketoverbindungen
DE10208007A1 (de) *	2002-02-26	2003-09-18	Forschungszentrum Juelich Gmbh	Verfahren zur Herstellung von Alkoholen aus Substraten mittels Oxidoreduktasen, Zweiphasensystem umfassend eine wässrige Phase und eine organische Phase sowie Vorrichtung zur Durchführung des Verfahrens
DE60315958D1 (de) *	2002-03-18	2007-10-11	Biocatalytics Inc	Alkohol-dehydrogenase mit hoher stabilität gegenüber lösungsmittel und temperatur
JP2004097208A (ja) *	2002-07-15	2004-04-02	Sumitomo Chem Co Ltd	３−ヒドロキシシクロヘキサノンの製造方法
DE10300335B4 (de) *	2003-01-09	2008-06-26	Iep Gmbh	Oxidoreduktase
DE10327454A1 (de) *	2003-06-18	2005-01-20	Juelich Enzyme Products Gmbh	Oxidoreduktase aus Pichia capsulata
AT413541B (de) *	2004-05-10	2006-03-15	Iep Gmbh	Verfahren zur herstellung von 2-butanol

2005
- 2005-09-23 AT AT0157005A patent/AT502185B1/de not_active IP Right Cessation
2006
- 2006-07-27 PT PT06762851T patent/PT1926821E/pt unknown
- 2006-07-27 US US12/067,752 patent/US20080233619A1/en not_active Abandoned
- 2006-07-27 CA CA2621306A patent/CA2621306C/en not_active Expired - Fee Related
- 2006-07-27 ES ES06762851T patent/ES2365159T3/es active Active
- 2006-07-27 EP EP06762851A patent/EP1926821B1/de not_active Not-in-force
- 2006-07-27 SI SI200631058T patent/SI1926821T1/sl unknown
- 2006-07-27 AT AT06762851T patent/ATE506446T1/de active
- 2006-07-27 DE DE502006009367T patent/DE502006009367D1/de active Active
- 2006-07-27 JP JP2008531549A patent/JP2009508499A/ja active Pending
- 2006-07-27 PL PL06762851T patent/PL1926821T3/pl unknown
- 2006-07-27 DK DK06762851.1T patent/DK1926821T3/da active
- 2006-07-27 WO PCT/EP2006/007425 patent/WO2007036257A1/de not_active Ceased
- 2006-07-27 CN CNA2006800350564A patent/CN101273136A/zh active Pending
2008
- 2008-04-23 KR KR1020087009691A patent/KR101345252B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
SI1926821T1 (sl)	2011-08-31
CA2621306A1 (en)	2007-04-05
KR101345252B1 (ko)	2013-12-26
AT502185A4 (de)	2007-02-15
DE502006009367D1 (de)	2011-06-01
EP1926821B1 (de)	2011-04-20
ATE506446T1 (de)	2011-05-15
CA2621306C (en)	2013-06-11
KR20080049136A (ko)	2008-06-03
JP2009508499A (ja)	2009-03-05
US20080233619A1 (en)	2008-09-25
WO2007036257A1 (de)	2007-04-05
AT502185B1 (de)	2007-02-15
PT1926821E (pt)	2011-07-27
PL1926821T3 (pl)	2011-09-30
CN101273136A (zh)	2008-09-24
DK1926821T3 (da)	2011-08-15
EP1926821A1 (de)	2008-06-04

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Wei et al.	2016	Engineering of a novel carbonyl reductase with coenzyme regeneration in E. coli for efficient biosynthesis of enantiopure chiral alcohols
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